Learn to Fly
by KathleenWinchester
Summary: Dean meets a hunter named Riley. She's trying to escape her past and get over the death of her uncle, and he's struggling with his feelings for Castiel. Dean and Riley become unlikely friends and realize that they're more alike than they know. Some Dean/OC, some Destiel. Rated for language and some smut.
1. Dead or Alive

**Author Note: So this is a story that's been bouncing around my head and I figured I better get it out :) I haven't written fanfiction in a long time and this is my first Supernatural story. There's going to be some Dean/OC and some Destiel, so if you're cool with that, carry on... -Kathleen**

* * *

 **Chapter 1 - Dead or Alive**

 _She's my cherry pie  
_ _Cool drink of water such a sweet surprise  
_ _Tastes so good makes a grown man cry  
_ _Sweet cherry pie_

Out of the hundreds of dive bars and strip joints Dean had been to over the years, he never got sick of this song. He grinned, taking a swig of his beer, eyes on the woman dancing on the bar in front of him. Tiny jean shorts, American flag halter, and cowboy boots.

Classic Americana.

Dean leaned back, content, enjoying the view and his drink. He and Sam had just finished a hunt that day and it would be a few more before they found another case. He'd dropped Sam off at the bunker and hit this bar, a few miles away, to blow off some steam.

 _I scream you scream  
_ _We all scream for her  
_ _Don't even try 'cause  
_ _You can't ignore her_

The girl on the bar laughed, sliding off the bar and rejoining her friends. Dean caught the eye of the woman across the bar from him, who raised her shot glass with a smirk. She had long, mahogany hair that fell in curls around her shoulders and over the back of her leather jacket. Slamming back the shot, she stood, slightly unsteady, walking toward the jukebox. Dean saw a flash of silver as she turned.

A hunter?

Dean was surprised. There weren't many that he hadn't met in the area, but that was definitely a blade tucked against her hip.

He smiled as he heard the next song come on.

 _It's all the same, only the names will change  
_ _Everyday it seems we're wasting away  
_ _Another place where the faces are so cold  
_ _I'd drive all night just to get back home_

He remembered that night with Sammy. That drive down to New Harmony, on what they thought would be Dean's last day on Earth. _Bon Jovi rocks, on occasion_ , he had told Sam. He had been staring death in the face, but he wanted to leave his brother with something to hold onto.

 _'Cause I'm a cowboy, on a steel horse I ride  
_ _I'm wanted dead or alive_

And what had followed... Forty years in hell, years of torture and inflicting pain on other souls... until Castiel had gripped him tight and raised him from perdition.

Cas.

Dean ordered a shot from the bartender. "Leave the bottle."

* * *

Dean stumbled against the Impala and pulled open the door. He sank down into the seat, his vision spinning slightly.

"Nope," he muttered as he tossed the keys into the glove box. "Not happening." He pulled his phone out of his pocket and sent a message to Sam.

 _Sleeping it off. Be home in the morning._

He threw the phone into the glove box next to his keys, slamming it shut and leaning back. Dean's head was spinning but at least his mind had shut the hell up. He looked up, out the window at the stars, and he thought of blue eyes, eyes like the heavens, eyes filled with stars...

"Goddamn son of a bitch!"

Dean jumped, looking out over the parking lot to see where the profanity was coming from. It sounded like some chick yelling at her boyfriend. _Entertainment._ Dean chuckled to himself. _Sweet._

"Are you fucking kidding me?" Around the corner came the hunter from earlier.

A gruff voice yelled from the bar. "Call a cab, sweetheart! Go home and sleep it off!"

The hunter walked past the Impala, still pissed but no longer yelling. "I don't live here, asshole!" She stopped at a beat-up Pontiac. "Come on, come on..." she muttered, pulling on the door handle. It didn't budge. "Fuck!" She kicked the front tire and turned around, leaning against the car. "Fuck."

Dean rolled down the window a crack. "You okay, there, darlin'?"

She seemed startled and her hand went in her jacket, no doubt holding the handle of her knife. She looked at Dean and sighed. "Yeah, I'm fine, I just..." She looked away, toward the bar. "The bartender took my keys. Told me to get a cab and come pick up my car in the morning. It's just... I don't live here. I don't know anyone around here and I was planning on crashing in my car for the night."

"That would explain the 'asshole' comment." Dean chuckled.

"Yeah." She pulled her leather jacket tight across her and crossed her arms.

"Maybe try a motel?" he offered.

She gave him a half-grin. "That would have been a great thought, had I not just drank the rest of my cash."

Dean looked behind him to the backseat, then back to her. He spoke despite his better judgment. "You, uh... you want to crash in the backseat?"

She looked at him warily. "It's... it's okay, you don't have to-"

"Seriously," Dean interrupted. He held up his hands. "No funny business or anything." He opened the door and stood up. The world spun a little and he blinked, then turned to the backseat, opening the door and shoving a couple of spare flannels off the seat. He saw an issue of Busty Asian Beauties and grinned, then stuffed it under the seat.

He turned back to her, motioning to the backseat. "See? It's not the Ritz, or anything, but it sure as hell beats the sidewalk."

She looked at him, quiet, considering. Finally, she nodded. "Okay." She stepped forward, looking him over and nodding again. "Thank you."

"Dean," he said, offering his hand.

She gave him a solid handshake, meeting his gaze. She was stronger than she looked, but that didn't surprise him. Her eyes were green and brown, with flecks of bronze that glinted in the moonlight. Dean realized he was staring and dropped his gaze. "I'm Riley."


	2. Family

**Author's Note: I've been trying to nail down when this would actually take place, and my thought is after Season 11, after (spoiler alert) Amara is gone and reunited with Chuck. It's AU, obviously, as if (again, spoiler alert) Mary didn't come back and the British Men of Letters haven't been in contact with the Winchesters. I hope that makes sense! And thanks for reading :D -Kathleen**

* * *

 **Chapter 2 - Family**

 _Her sister's eyes were huge, pleading. But it was too late. Riley looked down as her sister gasped, the blade pushing out through her stomach._

 _Riley screamed, pulling against the chains that bound her. "Sarah!" She could feel them biting into her skin but she didn't care._

 _The knife twisted and pulled back out, blood pouring down Sarah's shirt. Riley could hear it splatter on the concrete beneath them. "Sarah, it's okay. Just stay with me. You're going to be okay." Sarah's eyelids started to close and her eyes went blank. "No. No! Saraaaah!"_

Riley woke with a gasp, and before she knew what was happening her knife was at the throat of the man leaning over her.

"Whoa, hey..." He trailed off, holding up his hands and leaning back. "I was just trying to wake you up. You were having a bad dream."

Riley tried to catch her breath and took in her surroundings. She was in the back seat of a car outside the bar she'd been in last night. Outside the opposite window was her car. _Right._

She backed down, lowering the knife. "Sorry," she mumbled, embarrassed. She tucked the knife back against her hip and sat up, smoothing her hair. After a moment, she looked back up. The man was still staring at her.

"I'm sorry," she said, a little louder. She moved toward the door. "I'll get going."

"No, hey, uh... Let me take you to breakfast. There's a great diner down the street." She looked at him, curious. She had just pulled a knife on him... and he wanted to take her out to eat?

"Is that your normal response when a woman pulls a knife on you?" she challenged.

He grinned, laugh lines forming at the corners of his eyes. She found it strangely endearing. "You're not the only hunter who's jumpy when they first wake up."

She was taken aback. "Hunter? I'm not-"

"It's Riley, right?" She nodded, slowly, cautiously. "It's okay. My brother and I, we're hunters, too."

She suddenly remembered last night, when he introduced himself. She sat up, curious. "You said your name was Dean?" He nodded. "Are you... Dean Winchester?"

He tilted his head, grinning again, cocky. "The one and only." He raised his eyebrows. "So, we hittin' that diner, or what?"

Riley looked at him, considering, then nodded. "Let me go grab my keys from that asshole."

* * *

"So, where you heading?" Dean sat across from her in the booth. He shoved a huge bite of hash browns in his mouth.

Riley watched him, amused and a little queasy. "I don't know how you're eating so much already. My stomach's still pissed."

"Hangover cure," he said between bites. "Grease and starch is a cure-all. And you're avoiding the question." He raised his eyebrows, waiting.

Riley took a sip of her coffee. "South Dakota." She stared down into her mug. "I found out about a week ago that my uncle died." She paused. "I mean, not that he died a week ago. It's been awhile, apparently. I just... I just wanted to go and pay my respects."

Dean put down his fork. "Oh. Riley, I'm sorry. That's rough, losing family."

Riley looked up, hesitant. "I, uh, I think you knew him. At least, if you're the Dean he talked about." She took a breath. "His name was Bobby. Bobby Singer."

Dean stared at her, taking it all in. After a moment, he spoke. "You knew Bobby?" His voice was filled with emotion. "Bobby was your uncle?"

Riley nodded. "His younger sister, Elaine, was my mother."

Dean stared at her, still shocked. "I didn't know he had a sister."

"They weren't close. My mother was ten years younger than him, only a few years old when Bobby... When their dad died." Riley looked down again. They both sat in silence, remembering Bobby.

"Anything else I can get you two?"

Riley looked up, startled. She hadn't heard the waitress approach them. _Pay attention, Riley._ She smiled up at the waitress, reading her name tag. "Could I trouble you for another cup of coffee, Debbie?"

"Of course!" Debbie answered, reaching for the cup. Riley handed it to her, Debbie's hand brushing against Riley.

"Thank you, Debbie," Riley answered with an appreciative smile. Debbie turned, walking back to the front of the diner, and Riley watched her leave.

She turned back to Dean, who was staring with his mouth open. "You did not just do that."

Riley raised an eyebrow. "Do what?"

"You're... you... you were hitting on that waitress!" He looked equal parts confused and impressed.

Riley smirked. "Uh, yeah. Welcome to the twenty-first century."

Dean seemed lost for words. "No, I mean- I had a friend, she was- I just-"

"Oh my god." Riley tilted her head. "You were not just about to tell me you had a friend who was gay. You're actually killing me right now."

Dean blinked. "Well, not literally killing you."

Riley nodded. "Literally killing me. I can't. I can't even with you right now."

Dean looked at her for a moment, then back down to his plate, shrugging and taking a huge bite of sausage.

Riley started laughing.

"What?" he asked, confused.

She shook her head, trying to control her laughter. "Nothing..."

The waitress came back with Riley's coffee and slid the receipt onto the table, smiling at Riley.

"Thanks, darlin'," Riley said, taking a sip of the drink. The waitress walked away and Riley smirked at Dean. "See?" She lifted the receipt, showing Dean the bottom of it where the waitress had scrawled her phone number.

He nodded, clearly impressed. "Well done." He looked up at the clock behind Riley. It was almost noon. "So, you hittin' the road today?" Dean looked back at the waitress. "Or you gonna stick around, and, uh..." He raised his eyebrows suggestively.

Riley sighed, looking away. "I should probably get on the road before it gets dark. It's a good six hours to Sioux Falls." She took a sip of the coffee, finally starting to feel human again. "I don't know how many more nights I can sleep in the backseat of my car."

Dean considered that. "You know, I'd be doing Bobby a disservice if I didn't ask... Do you want a place to sleep tonight? We've got plenty of spare rooms, food, a hot shower..." Riley just looked at him, her expression blank. "You don't have to. If you just want to get going, I mean, I get that..." He trailed off, unsure.

She finally spoke, her voice quiet. "You don't have to do that."

"What are you talking about?" Dean shoved a piece of bacon in his mouth. "That settles it, then," he said, his words jumbled around the food. "You're coming home with me."


	3. Either Or

3 - Either Or

Dean pulled the Impala in front of the bunker and parked. Riley's Pontiac pulled in behind him, sputtering as she cut the engine. "You should really let me take a look at her before you go."

Riley laughed and closed her door, patting the hood of her car lovingly. "She can be a bit loud but she's in good shape. And Bobby-" Her voice caught. "I know enough to get by."

Dean out his hands up, surrendering. "Okay, okay. I didn't mean any offense." He started walking up toward the door and Riley swung her backpack over her shoulder, following.

Dean pushed the door open and Riley stopped in her tracks. "What the hell is this place?" She looked around, stunned. The building was massive and seemed to be primarily underground. It had a distinct Art Deco feel to it, and looking down the stairs Riley could see a huge table covered in a world map. More like Art Deco meets WWI.

"It belonged to the Men of Letters. Our grandfather was a member before the organization was destroyed." Dean seemed proud of his heritage. "My brother and I, we're legacies."

"It's absolutely incredible," Riley said, walking slowly down the stairs. "I had no idea the Men of Letters were real. I thought they were a myth."

"Dean? Is that you?" A voice called down the hall and a man emerged. He was tall, with broad shoulders and shaggy brown hair that fell just past his chin. "I was wondering when you were going to-" His eyes fell on Riley and he paused, brows furrowing. He looked back at his brother. "Dean?"

"Can I talk to you real quick, Sammy?" Riley stood, feeling awkward, as Dean crossed the room. They turned away from Riley, speaking softly. "I met her at the bar." Sam raised his eyebrows. "Nothing happened," Dean added quickly. "She's Bobby's niece."

"Bobby had a niece? I thought he was an only child." Sam looked over at Riley, who was looking away from them, apparently admiring the metalwork on the windows. He turned back to Dean.

"Well, I thought so, too. Turns out he had a younger sister. Riley's mom." He paused, looking over at her. "And she's a hunter." He looked back at Sam. "Look, she's on her way up to Sioux Falls and I offered her a bed for tonight. Sounds like she's just been sleeping out of her car."

Sam looked at Riley, then back at Dean, nodding. "Yeah, of course."

Dean looked back over at Riley. "Riley? This is my brother, Sam."

"Hey," she offered. "Nice to meet you, Sam."

"You, too." Sam gave her a shy smile, then looked at Dean. "You ready for lunch? I was just about to sit down and eat."

"Oh, definitely." Dean turned his head as he heard Riley laugh. "What?"

"You literally just ate."

"And?" Dean looked genuinely confused. Riley's stomach growled and her eyes went wide. "See?" Dean grinned. "Time for food."

"Do you mind if I hit the shower first? I think I still smell like a liquor cabinet." Riley ran a hand through her hair, a little uncomfortable. She wasn't used to letting people help her.

"Yeah, of course. There's a spare room down the hall, fourth door on the left," Dean answered, gesturing.

"Thanks," Riley answered softly, turning away and heading down the hall.

* * *

The hot water hit Riley's back and she let out a sigh. It had been too many weeks of coin-operated showers at trucker rest stops, too long since she'd had a proper shower.

She bowed her head, letting the stream hit her shoulders and her aching muscles. _Damn, this is nice._

Twenty minutes later, Riley stepped out of the shower, the tile cool against her bare feet. She wrapped a towel around herself and stepped to the mirror. She stared at her reflection. Her hair fell in dark waves past her shoulders and down her back. There was a thick, star-shaped scar on either shoulder and crisscrossing scars down her arms from countless fights with supernatural creatures.

Riley walked over to the bed, where she had laid out a clean set of clothes. A long-sleeved plum Henley, dark, straight-legged jeans that were torn at the knees, and a matching set of black bra and panties.

She heard a knock at the door and turned. "Riley?" Dean called, cracking the door and peeking in. "You decent?"

Riley grinned, walking over to him. "You know, after knocking, you should really wait for the other person to answer."

Dean cocked an eyebrow. "Uh, lunch is ready."

"You could have walked in on me on a compromising position." Riley was only screwing with him, but she liked how flustered he was getting. She dropped the towel. "Oops."

"I, um-" Dean glanced down but then quickly back up, eyes wide. "Uh..."

Riley took another step forward and they were almost touching. Dean looked like he was concentrating very hard on not looking down. She leaned in close to him, her hand up on the wall behind him. "So?"

He blinked at her. "Uh, so...?"

Riley grinned. "So, you going to go so I can get dressed?"

Dean looked confused. "But I thought- Aren't you... I mean, you... and the waitress?"

"It isn't always one or the other," Riley answered, walking back to the bed. She slipped into her panties and could feel Dean's gaze on her. She turned her head, meeting his gaze. "It doesn't have to be either or." She turned back the bed, pleased with herself. The road was lonely and she missed flirting. "Now, go!" she told him, laughing. "Or are you just going to stand there and watch me get dressed?"

Dean's eyes were wide and he turned, a little confused. "I'm... going to go," he said, closing the door as he left.

"I'll be right out!" Riley called, laughing.

* * *

Dean walked away, shaking his head. He wasn't sure what the hell that had been about, but he could tell Riley enjoyed getting a rise out of him. _Literally._

"Hello, Dean."

Dean stopped, his breath catching as he entered the room and saw Castiel. "Hey, Cas," he said nonchalantly.

They hadn't talked much since that last conversation in the Impala, shortly before they had finally defeated the Darkness. Dean hadn't thought he would make it out alive. Actually... he often felt that way. And many times, he had been right.

So much was left unsaid. And some of it shouldn't have been said.

 _"It was our best shot."_

 _"I was just trying to help."_

 _"And you do help, Cas, you know." Dean paused. "Sometimes, me and Sam, uh, we have so much going on, that we forget about everyone else."_

 _"Well, you do live exciting lives."_

 _"Yeah, that's one word for it." Dean felt at a loss for words. "But you're always there, you know?"_ In my heart. In my thoughts. _"You're the best friend we've ever had."_ But... somehow so much more.

 _Cas looked at him, tilting his head, questions in his eyes._

 _How could he explain the closeness he felt? "You're our brother, Cas, I want you to know that." Dean mentally kicked himself. That's not what he meant._

 _Their eyes met. Cas looked... almost sad. "Thank you."_

Dean realized he had been staring at Cas. He cleared his throat and turned away as he heard Sam walk in from the hallway.

"Hello, Sam," Castiel said, looking at Sam. The deep gravel of his voice sent shivers down Dean's spine. _What is up with me today?_

"So get this," Sam began.

Dean walked over to the bar and poured a drink as Sam continued. "Ever heard of Elk Point, South Dakota?" Dean shook his head, sipping the whiskey. "Less than two thousand within city limits."

"And?" Dean sat down and took a bite of his sandwich. "Isn't that Jody's territory?" he asked, his mouth full.

Sam's forehead creased and he put his laptop on the table, sitting. Cas sat down next to Dean, who took another sip of his drink.

Sam looked at the two of them for a moment but didn't say anything. He looked back down at his screen. "Jody's got Claire and Alex on a case in Nebraska."

"You guys going hunting?" Riley asked, sitting down next to Sam. _Damn, she is quiet._ Dean was used to his moose-sized brother walking around. She took a huge bite of the sandwich in front of her. "What's the case?" she asked between bites.

Castiel stared at her.

Riley was sitting across from him at the table. She raised her eyebrows and gave a little wave. "Hi."

"Who are you?" Cas asked bluntly, his voice serious. Pausing only a moment, he leaned forward and put two fingers to her forehead. Riley gave a small gasp. "You're kin to Bobby," he said, putting down his hand. She nodded, looking confused and a little scared. Castiel paused and added gruffly, "I'm sorry about your sister."

Riley scooted back in her chair. "Who the hell are you?"

"I'm an Angel of the Lord," Cas stated simply.

Riley just stared, looking alarmed.

Dean turned to Castiel. "You can't just do that to people, Cas. We talked about this."

Cas looked at Dean, tilting his head. "Is this the personal space issue?"

"You're inside their thoughts and memories, so I'd say, yeah. It's a personal space issue." Dean looked away. "Riley, this is Cas. Before you ask, yes, he's an actual Angel. Cas, this is Riley. She's Bobby's niece and a hunter." Dean looked around the table. "Are we done with the introductions?" Everyone was quiet. "Alright, Sammy, what do you got?"

Sam raised his eyebrows, then spoke. "Four people in Elk Point have gone missing in the last week. Witnesses reported glowing red lights around the time of the disappearances. Sounds like our kind of thing."

Riley glanced at Castiel suspiciously and spoke softly. "Elk Point? That's pretty close to Sioux Falls, isn't it?"

Sam nodded. "About an hour south of there."

"I could drive up there with you guys. It's on the way to Bobby's. Then after we take out whatever's taking off with people, we part ways." Riley looked from Sam to Dean. "I mean, I'm not trying to step on any toes" she added quickly. "If you guys prefer to hunt by yourselves, I can get out of your hair."

Dean looked at Sam, who shrugged. Dean nodded, looking at Riley. "We'd be glad to have you along. But," he added, "I promised you a night of sleep in an actual bed. So we'll go first thing tomorrow morning. Okay?" He asked, looking around at the three of them. It wasn't really a question.

Sam nodded. "I'll get the suits ready." He shot a pointed glare at Dean. "They still reek of beer from the last time you ironed them."

Dean grinned. "I don't know what you're talking about."


	4. Nightmares

**Chapter 4 - Nightmares**

Riley's hand trailed across book spines as she took in the massive room.

"You're welcome to read anything you like," a voice came from behind her. She turned and saw Sam standing in the doorway.

"I can't believe this place has a library. This is..." Riley shook her head in disbelief. "...incredible."

Sam ran a hand through his hair, looking around. "It is, isn't it? Sometimes I get so used to having all of this at our disposal... I think I forget how lucky we are."

"It's a hell of a collection." Riley turned back to the shelf in front of her. Old black leather hardbacks, some of the spines cracked and peeling. Some of the titles had worn off.

 _Malleus Maleficarum_

Riley pulled out the old, worn book and gently opened it. It seemed older than time. The pages were written in calligraphy and were incredibly ornate.

"That's the original manuscript by Heinrich Kramer," Sam told her. "Written in 1487."

She looked up at him, eyes wide. "You're serious?"

He nodded, smiling gently. He looked at her, studying her for a moment.

Riley was confused. "What is it?" She looked down at the book. "I can put it back, I-"

"No, no, that's not it," Sam told her, shaking his head. "It's just really nice to have someone else here who appreciates books. That's all."

Riley grinned. "Dean's not a big reader?"

Sam laughed. "Uh, no. Not if he can avoid it." He paused for a moment. "Well, I'll leave you to it. Nothing worse than someone chatting your ear off when you're trying to read. Enjoy," he said with a wave, walking out of the room.

Riley smiled to herself, shaking her head. It was strange, being here. It felt almost like... home.

* * *

 _Pain seared through Riley's shoulder as the angel blade pushed through her flesh. She clenched her jaw, biting back a scream as it made it through the other side. The demon grinned at her and pushed harder, lodging the blade in the wall._

 _"It can't kill me," she spat past gritted teeth. "I'm human."_

 _The demon's eyes flashed black for a moment. "The point was never to kill you." He pulled another blade from behind his back, running the tip gently down Riley's cheek. "The point," he said, drawing a thin line of blood across her collarbone, "is to make you hurt, the way you hurt my brother."_

 _Riley narrowed her eyes, breathing through the pain. Her shoulder throbbed with every little movement. "A demon who cares for anyone other than itself? Guess mom was right. You do learn something new every day."_

 _The tip of the blade reached her shoulder and the demon put pressure against it. It pierced her flesh, slowly, inch by inch._

 _Tears fell down Riley's cheeks but she wouldn't let herself scream. She closed her eyes, her breathing ragged._ You're not here, _she told herself_. You're outside, standing in the rain, looking up at the sky. You're-

 _Riley felt a slap across her face and she opened her eyes with a gasp. The demon grabbed her face in one hand. "No. You're staying here. With me. You're going to feel every-" He pushed the blade in farther. "Single." A sound escaped Riley's throat, a sound like a wounded animal. "Inch." The blade hit the wall. She was pinned from both sides._

 _"I'm going to kill you, Merrick." She saw stars on the edge of her vision and she blinked them away, taking a shuddering breath._

 _Merrick laughed, throwing his head back._

Riley opened her eyes, her breathing fast, taking in her surroundings, her hand finding the hilt of her knife under the pillow. She relaxed, seeing the room around her. The Men of Letters bunker.

Pulling on her jeans, she quietly opened the door and stepped into the hall. It was quiet, other than the ticking of the clock in what Sam and Dean had referred to as the War Room. She walked in and found the cart that held decanters of alcohol and tumblers. Classy. Pouring a shot into one of the glasses, she recapped the decanter and sipped the whiskey. It burned down her throat, leaving her with a warm feeling that pushed her dream further away.

"Nightmare?" Dean asked. Riley spun around and saw him standing in the doorway.

She gave a slight nod. "Hunter," she explained simply.

"Yeah, I'll give you that," Dean said, nodding and raising his eyebrows in agreement.

Riley took another sip and grinned at him. "Nice robe."

Dean looked down at himself. "I think I'm adorable."

Riley laughed suddenly, and it echoed in the empty room. She put a hand quickly over her mouth, grinning. "Oops," she whispered. Dean grinned back at her and walked to the cart, pouring himself a drink. She grabbed his hand, whispering, "Come with me," and pulling him toward her room.

Dean stopped wth a smirk, still holding her hand. "You going to keep your clothes on?"

Riley frowned at him. "Shut up." He made a face like, _Who, me?_ and she pulled him into the room, closing the door behind them. "I don't want to wake anybody up." She tipped her head back and downed the rest of her drink, putting the glass down on the bedside table, then sat on the edge of the bed.

"It's just Sammy. Cas left, but even if he hadn't, angels don't sleep," Dean told her. He raised his eyebrows, smirked, and finished off his whiskey.

"It's not a competition." Riley looked down and realized she was just in a tank top. She reached to the bedside table to grab a flannel shirt she had set out for the next day. As she looked up, she could see Dean looking at the three-pointed star-shaped scars on her shoulders.

"What the hell made that?" He caught her gaze and could tell that she was uncomfortable. "I'm sorry. I, uh- I don't usually ask about other people's scars. That's just... I've never seen anything like it before."

Riley put the shirt down, sitting back against the headboard and pulling her knees up against her chest. "No, it's okay," she said, her voice neutral. "They were made by angel blades."

Dean stared at her. "Son of a bitch."

Riley laughed a little. "Yeah, that's one way of putting it."

"But they don't work on humans." Dean frowned.

"No," she agreed. "Not in the way that they do on angels and demons. On a human, they're just a blade... A very _sharp_ blade."

Dean knitted his brows. "An _**angel** _ did this?" He shook his head. "I mean, they can be dicks, but-"

She cut him off. "No, I had never met an angel before today. It was..." She looked away. "A demon. He called himself Merrick."

Dean was quiet, almost respectful. Every hunter had their story, their baggage, their loss. It wasn't for the feeble-hearted. It would wear you down, day by brutal day.

Riley could feel the alcohol hitting her system. She wasn't intoxicated, but she felt warm and relaxed. She closed her eyes, laying back on the bed, her legs still dangling off the bed. "This is nice," she said. She opened her eyes, watching Dean lay down beside her. "It's nice not to have to explain everything."

"You've been on your own for a lot time, haven't you?" Dean asked, but he already knew the answer.

Riley turned, looking at him. Her face was an open book, and he could see in it how he had looked when Sammy had pulled Michael into the cage. When he thought that... that was it. Sammy was gone. He saw the loneliness, the emptiness, the failure to protect the one you were sworn to keep safe. He saw it all and suddenly he felt like he had known her for his whole life.

Riley's eyes drifted close, her mind clear for the moment. Dean could feel the tug of sleep and he closed his eyes. _Just for a moment_ , he told himself. _Then I'll go back to my room._

* * *

Riley woke, and she took a deep breath, her eyes still closed. She had slept deeply and dreamlessly. Sleeping in an actual bed had been bliss, the sheets and blanket so soft. She could feel the steady beating of-

She opened her eyes cautiously. Dean was still asleep, and what she had confused for an extremely firm pillow was in fact, his chest. She was curled against his body, his arm wrapped around her protectively.

Riley was torn between wanting to jump up and get a door between them, and just staying still, laying here for as long as he was asleep.

 _If I lay here_

 _If I just lay here_

 _Would you lie with me_

 _And just forget the world_

The lyrics came to her suddenly, and she mentally shook her head. _Get your ass up before he wakes up._ _That's the last thing you need... something else to hurt you. Someone else to let in._

She lifted his arm carefully and slid out from under him. Tiptoeing across the floor, she gently picked up her bag and went into the bathroom, quietly closing the door behind her.


	5. Sweetheart

A/N: Hopefully no one's having an issue with the way I shorten Castiel's name. I know people are very opinionated! :) I spell it the same way they do in the actual scripts (Cas), which Misha has talked about. I apologize if it's driving anybody crazy!

Thanks for reading :)

* * *

 **5 - Sweetheart**

 _Dean ran, Benny leading and Cas beyond him. He could hear the snarls of other creatures chasing them, but he knew they were almost there. Almost to the place where Purgatory was ripped open, splitting at the seams._

 _The earlier conversation played through his mind. He tried to push it away but failed. A hard knot formed in his stomach. Cas has to get out. I have to get him out._

 _"I don't think it will work for me." Cas glanced at Dean. Dean just stared back at him, his gaze steely, words unspoken._ It has to work. You have to come with me.

 _"You hear what he's telling you, Dean?" Benny's voice was unemotional. "Your buddy is saying-"_

 _Dean cut him off. "Listen to me, you undead blood junkie." Benny looked down. "I'm the one with the mojo, I'm the one with the plan. Cas?" He paused, staring at Castiel, face unapologetic. "We're gonna shove your ass back through the eye of that needle if it kills all three of us." Castiel stared at Dean, silent. Dean swallowed hard, not breaking Cas's gaze._ I will not leave you here.

 _They were at the seam. He could feel Benny's soul burning in his arm as he ran up the hill_

 _"Cas, come on!" he shouted, blue rays of light filling the forest around him. He turned back, feeling the pull of the seam behind him. He reached to Cas, offering his hand. "Come on!" Cas gripped his arm. "I got you, hold on!"_

 _"Dean!" Cas yelled, his eyes saying something that his voice couldn't._

 _"Hold on!" Dean shouted, but he could feel Cas slipping from his grip. Suddenly the seam pulled and Dean went flying through. His last image of Purgatory was Castiel, his blue eyes staring. Then the seam sealed around him, and his vision went dark._

"Cas!" Dean shouted. His heart pounded hard in his chest.

"Dean, you okay?" He opened his eyes and saw a green and bronze gaze staring back at him. The eyes seemed unfamiliar and he reacted suddenly, grabbing the person and flipping them onto the ground, pinning their shoulders and hips to the floor.

Riley stared back at him as she struggled to catch the breath he had knocked out of her. "You were... having a... bad dream," she managed to get out. "I was just trying... to wake you up."

Dean stared at her, still not awake, not understanding. "Dean?" He blinked. "Could you let me up?" Her voice sounded a little panicked, though her face was blank and unaffected. Almost too unaffected. He suddenly remembered her scars, what she had shared about the demon who had pinned her to the wall with angel blades and tortured her.

"Oh... Shit." He helped her up. "Sorry." Dean paused, looking her over. "You okay?"

"Yeah," Riley said, her voice steadier. "I'm fine." She frowned. "You okay? That was a hell of a dream you were having."

He shrugged. "Hunter." Riley gave him a nod, remembering their conversation the night before.

"Sam said he's ready to hit the road when you are," Riley told him.

Dean nodded. "Tell him I'll be there in ten."

* * *

Riley followed behind the Impala, hauling ass out of Kansas. They were still an hour away from Elk Point, but they'd make it by a little after noon. Plenty of time to talk to witnesses and follow any leads.

She stifled a yawn and took a gulp of her energy drink. _Any time now, caffeine. Feel free to kick the fuck in._

A song came on and Riley grinned. This was the iPod she and her sister had loaded with music for their last big road trip. She hadn't changed a single song on the playlist. Hell, she hadn't even plugged the damn thing into her laptop since Sarah had died.

Her breath caught for a moment. She took a slow, deep breath. One day, this would be normal. One day, it wouldn't hurt so bad. One day, it wouldn't feel like her heart had been ripped straight out of her chest, leaving a gaping, bleeding empty wound. Riley turned the music up louder, trying to drown out everything else.

 _I'm a red hot fox, I can take the knocks_  
 _I'm a hammer from hell, honey can't you tell_  
 _I'm the wild one_  
 _Yes, I'm the wild one._

* * *

Riley looked nervously at the Winchesters. She preferred hunting alone. It was easier when it was only your own hide you had to keep safe. Sam nodded and Dean gave the signal to move forward.

They approached the house where the creature had been holed up. Sam and Dean took the front door as Riley went around to the back. They had figured out that the missing people had been taken-and killed-by a will-o'-the-wisp. They came in many varieties but this one was straight out of England. It appeared as a glowing light and led people to their deaths, but during most of the day, it kept a human form. It was one of the fey, or fairy folk, and could be hurt by iron.

Riley gripped her dagger. It wasn't her usual folded steel knife and the hilt felt somehow heavier in her hand. She slowly reached out, testing the door handle. It was unlocked. She turned the knob cautiously, stepping into the room. It was clear.

She stepped carefully into the next room, scanning it quickly. It was a living room, the boarded windows letting slivers of light through, most everything covered in a thick coat of dust. There was an armchair facing an old tv and Riley crept toward it. She spun the chair, but it was empty.

"Looking for someone?" a voice asked. Riley spun and saw a man standing in the doorway. He had deep red hair and dark eyes. Suddenly he turned into a light form, the same deep red, flashing across the room toward Riley. She blinked and he had appeared in front of her. Before she had a chance to attack, he threw her against the wall. Shelves broke and fell on her as she slid to the floor. _Does everything have to have super fucking human strength?_ She clambered to her feet, sinking into a fight stance, ready for the next attack. It flashed toward her and she turned, predicting its move. Just as it turned corporeal she sunk the iron dagger into its torso. Red light poured out of the wound. She could feel the knife move against bone and muscle as she ripped it back out. The creature gave a shrill cry as it burst into light and disappeared.

Riley stood, catching her breath. The house was still for a moment, and then came a crash from the front of the house. _Wait. There were more?!_ She ran toward the noise, confused. Normally will-o'-the-wisp lived and killed alone. They were a solitary creature.

Pushing through a door she entered a study just in time to see Sam hit the window. It shattered and he slammed through it, falling into the deck outside.

"Sammy!" Dean yelled, pushing himself to his feet. It seemed he had been the cause of the earlier crash.

"I'm okay," Sam's voice came from outside.

Riley's eyes met Dean's. "Where'd it go?" she asked. They looked around the room, but it was empty. Suddenly a flash of light came from behind Riley and she whipped around.

A grabbed Riley's throat, lifting her up off her feet. She grabbed onto the hand, trying to relieve the pressure, struggling. This was a woman, older than the other wisp Riley had killed. It hissed at her, dark eyes glowing like embers. "You killed my son."

She could hear Dean moving toward them but the creature lifted a hand and he went flying back again. She heard the sound of glass crunching under boots but she wasn't going to wait for someone to rescue her.

Riley sucked in what little air she could and let go, her windpipe closing completely. She had a moment of panic but pushed it aside and slammed the dagger into the mother. It screamed and burst into red light. Riley dropped to the ground and struggled to catch her breath. "Yeah, well, your son was a dick," she muttered, the red light of the mother already fading. She coughed, her throat feeling sore.

"Not too bad, sweetheart," Dean said, offering Riley a hand. She took it, standing, and frowned at him.

"Not too bad?" She laughed. "I just saved your ass, sweetheart."

Sam laughed loudly as he stepped back through the window and into the room. Dean shot him a look and Sam shrugged. "What? She did."

Riley grinned at Dean. "Now buy me a damn drink."


	6. No Strings

A/N: I have no good apology for the two month wait other than... life. Things kind of got away from me and... now it's October. Well, fuck.

Thank you to everyone reading (despite my hiatus) and thanks especially to the five people who have Alerts for this story! You literally make my day every time you're still there.

Hopefully, this chapter will make up for the very late update. And I promise, more updates very soon!

* * *

"You guys can not be serious!" Sam stared, looking from Dean to Riley.

"Four?" Dean asked, ignoring his brother.

Riley shook her head, grinning. "Six." The bar was loud and raucous around them.

"You're both going to end up with alcohol poisoning. I'm not dragging your asses to the hospital!"

"I mean, six shots to start," Riley continued.

"Unbelievable." Sam sighed, turning away.

Dean grinned. "You, uh, sure you can handle-"

"Do not even," Riley interrupted. "Let's get this straight." She paused, the corner of her mouth creeping up in a grin. "There's a joke there, but I'm going to leave it alone." She cleared her throat. "I'm grown. I know how to handle myself and I know how to hold my liquor. Will you go get the damn shots already?! I am entirely too sober right now."

Dean laughed, shaking his head and walking away toward the bar. "Dean?" He turned back as he heard Riley call to him. "No tequila, okay? I'll black out and it won't be pretty." Sam groaned and Dean gave a mock salute and grinned, turning back toward the bar. This was going to be a good night.

* * *

Riley stumbled back toward the table and fell into the booth clumsily, leaning against Dean. "It's up next!" she whispered loudly. Sam had left them a few hours ago, rolling his eyes as they goaded each other on, both Dean and Riley drinking a God-awful amount, but promising to find the three of them a motel room next door.

"This is not going to work," Dean told her. His half-lidded eyes betrayed him and Riley laughed.

"You're drunk," she proclaimed.

"Takes one to know one," he replied childishly.

"Sssshhh," she chided. The track changed and Warrant's "Cherry Pie" started playing. "Just watch! Drunk girls cannot resist this song."

Dean thought for a moment, his brows creasing, and looked back at her. "You're a drunk girl."

Riley frowned. "Shut up." She looked away, watching the bar. Slowly, she grinned, looking back at Dean. "Told you."

Dean looked over and saw a trio of girls climbing onto the bar. His jaw dropped and Riley laughed. "You're welcome."

She leaned back, enjoying the feeling of carelessness and the warmth radiating from her stomach. There was nothing like drinks after a good hunt. Riley had run into other hunters in the past that didn't like the job. They resented it. They looked for a way out of the life. But, that wasn't Riley. This was what she was made for. This is what she lived for. She was a hunter.

The song ended and the bartender called last call. Riley sat up. "Time to get out of here. It's about to get real desperate, real fast."

"And?" Dean asked, raising his eyebrows with a grin.

Riley rolled her eyes. "You're not desperate. You're just drunk."

Dean laughed and they slid out of the booth, swaying a bit as they stood.

"You all right there, Winchester?" Riley feigned concern. "You sure you can handle your liquor?"

Dean frowned at her, but it was short-lived. "Real funny," he said, grinning despite himself.

They made their way through the dwindling crowd, pushing through the doors and stepping into the cool night air. Riley laughed, turning toward Dean, walking backward as she talked. "You know, sometimes I worry about liver damage... but then I figure, the odds of me living long enough for my liver to crap out on me are pretty much zilch at this point." She turned back around, taking long, slow strides as she walked. "It's not like you meet a lot of old hunters."

Dean laughed. "Well, you're not wrong there. Kind of dark, though."

Riley shrugged, glancing back at him. "Dark, maybe. I see it as more realistic. We only get so much time. Might as well use it while we've got it, you know?"

Dean paused as they reached the Impala, parked outside the motel. "Sammy said he'd leave a key in the glove box," Dean told her as he rooted around in it.

Cassette tapes and old registration papers fell out as he looked. He sat down on the passenger side to get a better look.

"Jesus, Dean, your glove box is a mess." Riley leaned over him, trying to help search.

"I don't go into your car and start criticizing-," Dean muttered just as Riley's foot slipped and she fell on him suddenly. His candy apple green eyes found her forest and bronze gaze, their faces close.

Riley's breath caught and she couldn't move for a moment. She saw his eyes dart to her lips. Fuck it, she thought, and their mouths clashed together and her ability to think flew straight out the window.

Their lips met, hungry, their hands pulling each other closer. Riley straddled Dean and the friction of their jeans made Dean groan.

Riley paused, breathing hard, her dark curls cascading around their heads. "Just sex, okay? We're not going to cuddle, we're not going to have breakfast together. No strings. Deal?"

Dean was taken aback. He was usually the one giving 'the talk.' He nodded, trying and failing to catch his breath. "Deal."

Their mouths met again and Riley gasped as she felt his teeth graze her bottom lip. She climbed off of him and they stood, hands pulling at each other, fingertips sliding under shirts and pulling at the layers of clothing between them.

Dean pushed Riley up against the Impala, as he pulled her shirt over her head. She gasped, the cold metal against her back as his lips found her neck. A shiver went down her spine and her eyes closed as he kissed down her neck to her collarbone. His tongue darted, finding the hollow beneath his lips.

Riley's fingertips explored the ripple of muscles under his skin, beneath his t-shirt. She traced the lines of his back; his shoulder blades, ribs, then coming to the small of his back where his jeans were slung low. She pulled him against her, grinding against him. He gasped against her shoulder and she could feel him already growing hard.

Her eyes opened, meeting his. "Backseat?" She nodded, breathing hard. He pulled the door open and she climbed inside, leaning back and unbuttoning her jeans. He pulled her boots off and she lifted her hips, helping him pull off her jeans and panties. He pulled off his shirt and unbuttoned his jeans as she unclasped her bra, and he climbed onto the seat, closing the door behind him.

"You have a-" she asked as he nodded.

"Yeah," he said, pulling a condom out of the back pocket of his jeans. "You're sure?" he asked, his voice serious.

She nodded. "Yeah." She helped him pull his jeans off and ripped open the condom wrapper. She wrapped her hand around him, feeling his girth, stroking him a few times, and he leaned back against the door. She slid the condom over the length of him and he let out a moan. His eyes fluttered open and he sat up, pulling her close, their mouths finding each other once more. His hand slid between them, finding her already wet and ready for him. He moved a fingertip against her core and her eyes closed, a low moan falling from her lips. He moved against her again, keeping a steady rhythm. She moved with him, her hips keeping time, her back arching as his name escaped her lips.

"Dean..."

Her hand reached between them and she found him, stroking his member and helping guide him. She felt the tip of him at her entrance and they paused, their mouths close together, lips almost touching. Slowly, Dean sank into her, an inch at a time, until he was fully sheathed inside her. They both gasped at the feeling, and her eyes flew open. She sat up, wrapping her arms around his shoulders, their chests pressed close together. She started moving, finding a steady rhythm, and his hands went to her hips, pulling her harder against him.

She picked up the pace, following his lead. Their breath had fogged all of the windows, granting them some much-needed privacy. Dean leaned forward, laying her down on the seat. Her hips rose to meet every thrust, and she could feel an orgasm building.

"Almost," she gasped. Dean nodded, holding himself over her as he moved. His fingertip found her core again and she felt herself coming closer to that edge. "Dean..."

She gasped and he thrust harder, filling her completely. She gripped him tight, her vision exploding into stars as she closed her eyes and waves of pleasure washed over her.

He thrust a few more times and came hard, her body still pulsing, milking him of every drop.

They stayed like that until both their breathing slowed. Dean's eyes opened and he slowly pulled out of her. Riley moaned softly at the feeling. He collapsed next to her.

"Fuck," Riley said, shaking her head.

Dean laughed gently. "Yeah."


End file.
